PRACTICAL ORGANIC CHEMISTRY PREPARATION 20. CHg.NHa.HCl Q-lycocoll Ester Hydro chloride, \ CO.OC2H- Klages, Ber., 1903, 36, 1506, Hantzsch and Silberrad, 1900, 33, 70. 250 c.c, formaldehyde solution (40 per cent.). 90 grams ammonium chloride (powdered). 1 10 „ potassium cyanide (in 200 c.c. water). 63 c.c. glacial acetic acid. " The first part of the process consists in the preparation of methyleneamino-acetonitrile. The formaldehyde and ammonium chloride are mixed in a wide-necked glass jar cooled in a freezing mixture and stirred by means of a stirrer as shown in Fig. 64. When the temperature falls to 5° the potassium cyanide solution is slowly run in from a tap-funnel during three hours, the temperature being maintained below 10°. When half the cyanide solution has been added the ammonium chloride will have com- pletely dissolved. Whilst the second half of the solution is being added, 63 c.c. of glacial acetic acid are dropped in from another tap-funnel at about the same rate, whilst the tempera- ture is kept below 15°. As soon as the acetic acid is added a white 'crystalline substance begins to separate and gradually fills the liquid. The stirring is continued for another hour after the solutioris have been added. The crystalline mass is filtered, washed with water and dried. The yield is 60 — 70 grams. Methyleneamino-acetonitrile melts at 1 29°. 1 1 m ay be recrystallised from alcohol, but is usually pure enough for further treatment. On hydrolysis in presence of alcohol it breaks up into glycocoll ester hydrochloride, ammonium chloride and formaldehyde. CH2:N. CH2CN + 2H2O + C2H5OH -I- HC1 = (HCl)NHa, CH0. COOC,HB + NH4C1 + CH20. Twenty-five grams methyleneamino-acetonitrile are added to 170 c.c. of absolute alcohol previously saturated in the cold with hydrogen chloride.